Process for producing optically active beta-trifluoromethyl-beta-hydroxycarbonyl compound
a trifluoromethyl and beta-hydroxycarbonyl technology, applied in the preparation of carbonyl compounds, organic chemistry, chemistry apparatus and processes, etc., can solve the problems of insufficient industrial processes, large sensitivity to polymerization, and process that requires the equivalent amount of a relatively expensive chiral auxiliary group, etc., to achieve stable hydrate, high yield, and high asymmetric induction
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[0061]The present invention will be illustrated in greater detail with reference to the following Examples, but the invention should not be construed as being limited thereto. As acetone, anhydrous acetone having water content of 0.005% at the maximum (manufactured by Kanto Chemical Co., Inc.) was used.
examples 1 to 15
[0062]The results obtained in Examples 1 to 15 are summarized in Table 1. All the Examples were carried out in a similar manner. Examples 3 and 8 are shown below as representatives.
[0063]
TABLE 1Exam-ReactionReactionYield ofr.y. ofple12a.c.*asolventTemp.*btime3*ca.c.*de.e. of 3*e11a (R = C2H5)2aS-(l)-prolineDMSO*fRoom48 hours96%Not3a (R1 = H, R2 = CH3)(R1 = H, R2 = CH3)0.3 mmoltemperatureconducted3% e.e., R21a (R = C2H5)2aS-(l)-prolineTHF*gRoom48 hours19%Not3a (R1 = H, R2 = CH3)(R1 = H, R2 = CH3)0.3 mmoltemperatureconducted37% e.e., R31a (R = C2H5)2aS-(l)-prolineCH3CNRoom48 hours64%Not3a (R1 = H, R2 = CH3)(R1 = H, R2 = CH3)0.3 mmoltemperatureconducted42% e.e., R41a (R = C2H5)2aS-(l)-prolineCH2Cl2Room48 hours45%Not 3a (R1 = H, R2 = CH3)(R1 = H, R2 = CH3)0.3 mmoltemperatureconducted48% e.e., R51a (R = C2H5)2aS-(l)-prolineBenzeneRoom48 hours32%Not3a (R1 = H, R2 = CH3)(R1 = H, R2 = CH3)0.3 mmoltemperatureconducted52% e.e., R61a (R = C2H5)2aS-(l)-prolinen-HexaneRoom48 hours19%Not3a (R1 = ...
example 3
[0064]To an acetonitrile solution (amount of acetonitrile: 8 ml) containing 35 mg (0.3 mmol, 0.3 eq.) of S(1)-proline and 2 ml (1.6 g, 27.2 mmol, 27.2 eq.) of acetone was added 144 mg (1.0 mmol, 1 eq.) of a fluoral equivalent represented by the following formula:
[0065]
and the whole was stirred at room temperature for 48 hours. A saturated saline solution was added to the reaction mixture after completion of the reaction and the resulting mixture was extracted with diethyl ether. The recovered organic layer was washed with a saturated saline solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
[0066]To the residue was added 146 mg (1.0 mmol, 1.0 eq.) of α,α,α-trifluorotoluene as an internal standard substance, followed by 19F-NMR measurement. Based on relative intensity in the integration curve, the yield of the optically active β-trifluoromethyl-β-hydroxycarbonyl compound represented by the following formula:
[0067]
was calculated and found to be 64%....
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